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Quinic acid lactone derivative preparation method

A technology of ethyl acetate and isopropyl acetate, applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of low solubility, large demand for compound 1, and low reaction yield

Inactive Publication Date: 2016-03-09
CINKATE PHARM TECH SHANGHAI CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the solubility of toluene to compound 1 is relatively low, so the reaction yield is low
However, the target product calciferol needs to be obtained from compound 1 through more than 10 steps of operation, so the demand for this step of compound 1 will be large

Method used

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  • Quinic acid lactone derivative preparation method
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  • Quinic acid lactone derivative preparation method

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preparation example Construction

[0061] The present invention provides a preparation method of compound 2 shown in the following formula, characterized in that it comprises steps:

[0062]

[0063] (i) in an organic solvent, react with compound 1 to obtain compound 2;

[0064] Wherein, the organic solvent is selected from the group consisting of n-hexane, cyclohexane, DMF, ethyl acetate, isopropyl acetate, dichloroethane, or combinations thereof.

[0065] In the formula, R 2 , R 3 Each is independently selected from the following group: H, C1-C6 alkyl, or silicon protecting group; preferably, the silicon protecting group is selected from the following group: TBDMS-OTf, TIPS-OTf, or TES-OTf .

[0066] In another preferred example, R 2 for H, R 3 is H or alkyl.

[0067] In another preferred example, the organic solvent is a mixed solution of DMF and cyclohexane.

[0068] Said reaction can optionally be carried out in the presence of a suitable dehydrating condensation agent. In a preferred embodiment...

Embodiment 1

[0118]

[0119] Using compound 1 as a starting material, compound 1 was added into n-hexane, and the catalyst p-toluenesulfonic acid was added, and reacted at 90° C. for 18 hours. The reaction is shown in formula 12, and the synthesis from compound 2 to compound 3 is carried out with reference to WO2010 / 120698A1. The two-step yield was 25%. where R 1 for TBDMS, R 2 for H, R 3 for H.

Embodiment 2

[0121]

[0122] Using compound 1 as a starting material, compound 1 was added to a mixture of DMF and n-hexane, and a catalyst p-toluenesulfonic acid was added, and reacted at 90° C. for 18 hours. The reaction is shown in formula 13, and the synthesis from compound 2 to compound 3 is carried out according to the method disclosed in PCT application WO2010 / 120698A1, and the two-step yield is 48%. where R 1 for TBDMS, R 2 for H, R 3 for H.

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Abstract

The present invention relates to a quinic acid lactone derivative preparation method, which comprises: in an organic solvent, carrying out a reaction with a compound 1 to obtain a compound 2. According to the method of the present invention, the solubility of the reactant in the solvent is increased so as to substantially improve the yield of the product and provide convenience and economy. The structures of the compounds 1 and 2 are defined in the specification.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular, the invention provides a method for preparing calcidol compound lactonization intermediate fragments. Background technique [0002] Calciferol compounds are suitable for the prevention and treatment of osteoporosis, nephrogenic bone disease (nephrotic rickets, hyperparathyroidism (with bone disease), hypoparathyroidism, rickets and rickets caused by nutritional and absorption disorders). Osteomalacia, pseudocalcium deficiency (D-dependent type I) rickets and osteomalacia, etc. [0003] Because of its efficacy and effects, the calciferol compounds have a great market demand. However, if calcidol compounds are to be mass-produced, there will be a large demand for upstream intermediates, and there is an urgent need in this field for methods that can improve the preparation efficiency of upstream intermediates and simplify the process flow. [0004] [0005...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07C401/00
CPCY02P20/55
Inventor 赵立辉肖春荣刘娜周舸薛萍袁西伦肖飞
Owner CINKATE PHARM TECH SHANGHAI CO LTD
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